Synthesis of novel dipeptide sulfonamide conjugates with effective carbonic anhydrase I, II, IX, and XII inhibitory properties

Bugday N., Kucukbay F. Z., KÜÇÜKBAY H., Bua S., Bartolucci G., Leitans J., ...Daha Fazla

BIOORGANIC CHEMISTRY, cilt.81, ss.311-318, 2018 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 81
  • Basım Tarihi: 2018
  • Doi Numarası: 10.1016/j.bioorg.2018.08.032
  • Dergi Adı: BIOORGANIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.311-318
  • Anahtar Kelimeler: Carbonic anhydrase, Inhibitor, Homosulfanilamide, Dipeptide, Conjugate, BIOCHEMICAL-CHARACTERIZATION, PORPHYROMONAS-GINGIVALIS, BIOLOGICAL EVALUATION, AMINO-ACIDS, DERIVATIVES, ANTIBACTERIAL, DESIGN, ANTICANCER, PEPTIDES, BIOASSAY
  • İnönü Üniversitesi Adresli: Evet

Özet

Twenty-four novel sulfonamide derivatives incorporating dipeptide tails were synthesized by facile acylation reactions of homosulfanilamide through benzotriazole or dicyclohexyl carbodiimide (DCC) mediated coupling reactions. The carbonic anhydrase (CA, EC 4.2.1.1) inhibitory activity of the new compounds was assessed against four human (h) isoforms, hCA I, hCA II, hCA IX and hCA XII. Most of the synthesized compounds showed good in vitro carbonic anhydrase inhibitory properties, with inhibition constants in the low nanomolar range. Particularly, the new dipeptide-sulfonamide conjugates incorporating Ala, Phe and met in the dipeptide sequence, showed the most effective inhibitory activity against to CA IX and XII.